Chemistry and Biology of
Reactive Species
Prof. Harinath Chakrapani Lab
Home > Publications
2025
Publications
2021
2024
Intracellular peroxynitrite perturbs redox balance, bioenergetics, and Fe-S cluster homeostasis in Mycobacterium tuberculosis
2021
Redox Biology, 2024
2024
An Esterase-Cleavable Persulfide Donor with No Electrophilic Byproducts and a Fluorescence Reporter
Bharat Choudhary, T. Anand Kumar, Akshi Vashishta, Sushma Tejashri, Amal S Kumar, Rachit Agarwal and Harinath Chakrapani
2021
ChemComm, 2024
2023
β-Galactosidase-activated nitroxyl (HNO) donors provide insights into redox cross-talk in senescent cells
Laxman R. Sawase, T. Anand Kumar, Abraham B. Mathew, Vinayak S. Khodade, John P. Toscano, Deepak K. Saini and Harinath Chakrapani
2021
ChemComm, 2023
2023
Intracellular Accumulation-Driven Potentiation of Moxifloxacin Against non-replicating drug-tolerant Mycobacterium tuberculosis through a Prodrug
T. Anand Kumar, Piyali Mukherjee,M. SharathChandra, Shalini Birua, Grace Kaul, Abdul Akhir, Sidharth Chopra, ProfileJennifer Hirschi, Amit Singh, Harinath Chakrapani
2021
BioRxiv, 2023
2023
Laxman Sawase, Jishnu C.V., Suman Manna and Harinath Chakrapani.*
2021
ChemComm, 2023
2022
Somnath Shee, Samsher Singh, Ashutosh Tripathi, Chandrani Thakur, T. Anand, Mayashree Das, Vikas Yadav, Sakshi Kohli, Raju S Rajmani, Nagasuma Chandra, Harinath Chakrapani, Karl Drilca, Amit Singh.
2021
Antimicrobial Agents and Chemother, 2022
2022
Enhancing cellular sulfane sulfur through β-glycosidase-activated persulfide donors: mechanistic insights and oxidative stress mitigation
Prerona Bora, Manjima B. Sathian and Harinath Chakrapani*.
2021
ChemComm, 2022
2021
Leveraging an Enzyme/ Artificial Substrate System to Enhance Cellular Persulfides and Mitigate Neuroinflammation
Prerona Bora, Suman Manna, Mrutyunjay Nair, Rupali R. M. Sathe, Shubham Singh, Venkata Sai Sreyas Adury, Kavya Gupta, Arnab Mukherjee, Deepak Kumar Saini, Siddhesh S Kamat, Amrita B. Hazra* and Harinath Chakrapani*.
2021
Chem. Sci., 2021
2021
Fatty acid chain length drives lysophosphatidylserine-dependent immunological outputs
Neha Khandelwal, Minhaj Shaikh, Amol Mhetre*, Kithiganahalli Narayanaswamy Balaji,Harinath Chakrapani*, Siddhesh S. Kamat*
2020
Cell Chem. Biol., 2021
2020
Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO2) Donors
Dr. Satish R. Malwal, Dr. Kundansingh A. Pardeshi, and Dr. Harinath Chakrapani*
2021
ChemBioChem 2020, 21, 1–6
2019
2019
Carbonyl Sulfide (COS) Donor Induced Protein Persulfidation Protects against Oxidative Stress
Preeti Chauhan, Kavya Gupta, Govindan Ravikumar, Deepak Saini, and
Harinath Chakrapani*
Chem.Asian J. 2019, 14, 4717 –4724
Chemoproteomics of an Indole-Based Quinone Epoxide Identifies Druggable Vulnerabilities in Vancomycin-Resistant Staphylococcus aureus
Amogh Kulkarni, Isha Soni, Dhanashree S. Kelkar, Allimuthu T. Dharmaraja, Rathinam K. Sankar, Gaurav Beniwal, Abinaya Rajendran, Sharvari Tamhankar, Sidharth Chopra, Siddhesh S. Kamat, and Harinath Chakrapani*
J. Med. Chem. 2019, 62, 6785−6795
Targeted Antibacterial Activity Guided by Bacteria-Specific Nitroreductase Catalytic Activation to Produce Ciprofloxacin
Kundansingh A. Pardeshi, T. Anand Kumar, Govindan Ravikumar, Manjulika Shukla,
Grace Kaul, Sidharth Chopra, and Harinath Chakrapani*
Bioconjugate Chem. 2019, 30, 751−759
Photocontrolled endogenous reactive oxygen species (ROS) generation
Ajay Kumar Sharma, Harshit Singh, and Harinath Chakrapani *
Chem. Commun., 2019, 55, 5259-5262
A chemical–genetic screen identifies ABHD12 as an oxidized-phosphatidylserine lipase
Dhanashree S. Kelkar, Govindan Ravikumar, Neelay Mehendale, Shubham Singh, Alaumy Joshi , Ajay Kumar Sharma , Amol Mhetre , Abinaya Rajendran , Harinath Chakrapani , and Siddhesh S. Kamat
Nature Chemical Biology, 2019, 15, 169–178
2019
2018
A Vinyl-Boronate Ester-Based Persulfide Donor Controllable by Hydrogen Peroxide, a Reactive Oxygen Species (ROS)
Prerona Bora, Preeti Chauhan, Suman Manna, and Harinath Chakrapani*
Org. Lett. 2018, 20, 7916−7920
Redox‐guided small molecule antimycobacterials
Amogh Kulkarni, Ajay Kumar Sharma, and Harinath Chakrapani*
IUBMB Life 2018, 70, 826-835 (Invited Review, Special Issue on New Advances in Tuberculosis Drug Discovery and Therapy)
Reactive Oxygen Species-Triggered Tunable Hydrogen Sulfide Release
Preeti Chauhan, Swetha Jos, and Harinath Chakrapani*
Org. Lett. 2018, 20, 3766−3770
Visible-Light Controlled Release of a Fluoroquinolone Antibiotic for Antimicrobial Photopharmacology
Pooja Kumari, Amogh Kulkarni, Ajay Kumar Sharma, and Harinath Chakrapani*
ACS Omega 2018, 3, 2155−2160
Small molecule generators of biologically reactive sulfur species
Prerona Bora , Preeti Chauhan , Kundansingh A. Pardeshi, and Harinath Chakrapani*
RSC Adv., 2018, 8, 27359-27374
2018
Esterase Sensitive Self-Immolative Sulfur Dioxide Donors
Kundansingh A. Pardeshi, Govindan Ravikumar, and Harinath Chakrapani*
Org. Lett. 2018, 20, 4−7
2018
Visible-Light-Triggered Uncaging of Carbonyl Sulfide for Hydrogen Sulfide (H2S) Release
Ajay Kumar Sharma, Mrutyunjay Nair, Preeti Chauhan, Kavya Gupta,Deepak K Saini, and Harinath Chakrapani*
Org. Lett. 2017, 19, 4822−4825
2018
FLUORO/NO: A Nitric Oxide Donor with a Fluorescence Reporter
Govindan Ravikumar, Meisam Bagheri, Dr. Deepak Kumar Saini, and Dr. Harinath Chakrapani*
ChemBioChem2017, 18, 1529 –1534
2018
A small molecule for theraNOstic targeting of cancer cells
Govindan Ravikumar, Meisam Bagheri, Deepak Kumar Saini, and Harinath Chakrapani*
Chem. Commun., 2017, 53, 13352-13355
2018
Synergistic Activities of Nitric Oxide and Various Drugs
Govindan Ravikumar and Harinath Chakrapani*
Novel Biomedical Applications and Perspectives, 2017, Pages 293-312
2018
“On demand” redox buffering by H2S contributes to antibiotic resistance revealed by a bacteria-specific H2S donor
Prashant Shukla, Vinayak S. Khodade, Mallojjala SharathChandra, Preeti Chauhan, Saurabh Mishra, Shivakumara Siddaramappa, Bulagonda Eswarappa Pradeep, Amit Singh and Harinath Chakrapani*
Chem. Sci., 2017, 8, 4967–4972
2016
2018
Esterase Activated Carbonyl Sulfide/Hydrogen Sulfide (H2S) Donors
Preeti Chauhan, Prerona Bora, Govindan Ravikumar, Swetha Jos, and Harinath Chakrapani*
Org. Lett. 2017, 19, 62−65
2018
A Small Molecule for Controlled Generation of Peroxynitrite
Org. Lett. 2016, 18, 1274−1277
2015
2018
Mycobacterium tuberculosis has diminished capacity to counteract redox stress induced by elevated levels of endogenous superoxide
Free Radical Biology and Medicine, 84, 344-354
2018
Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors
Kundansingh A. Pardeshi, Satish R. Malwal, Ankita Banerjee, Surobhi Lahiri, Radha Rangarajan and Harinath Chakrapani*
2018
Benzosulfones as photochemically activated sulfur dioxide (SO2) donors
Satish R. Malwal and Harinath Chakrapani *
Org. Biomol. Chem., 2015, 13, 2399-2406
2014
2018
Site-directed delivery of nitric oxide to cancers
Nitric Oxide 2014, 43, 8−16
2018
Substituent Effects on Reactive Oxygen Species (ROS) Generation by Hydroquinones
Allimuthu T. Dharmaraja, Charu Jain, and Harinath Chakrapani*
J. Org. Chem. 2014, 79, 9413-9417
2018
Bioreductively Activated Reactive Oxygen Species (ROS) Generators as MRSA Inhibitors
Vinayak S. Khodade, Mallojjala Sharath Chandra, Ankita Banerjee, Surobhi Lahiri, Mallikarjuna Pulipeta, Radha Rangarajan, and Harinath Chakrapani*
ACS Med. Chem. Lett. 2014, 5, 7, 777–781
2018
Arylboronate Ester Based Diazeniumdiolates (BORO/NO), a Class of Hydrogen Peroxide Inducible Nitric Oxide (NO) Donors
Allimuthu T. Dharmaraja, Govindan Ravikumar, and Harinath Chakrapani*
Org. Lett. 2014, 16, 10, 2610-2613
2018
A phenacrylate scaffold for tunable thiol activation and release
Rathinam K. Sankar, Rohan S. Kumbhare, Allimuthu T. Dharmarajaa and Harinath Chakrapani*
Chem. Commun., 2014,50, 15323-15326
2018
A highly selective sulfinate ester probe for thiol bioimaging
Satish R. Malwal, Ajay Labade, Abhijeet S. Andhalkar, Kundan Senguptaa and Harinath Chakrapani*
Chem. Commun., 2014,50, 11533-11535
2013
2018
A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)
Allimuthu T. Dharmaraja, and Harinath Chakrapani*
Org. Lett. 2014, 16, 2, 398-401
2018
Nitroreductase-activated nitric oxide (NO) prodrugs
2018
INDQ/NO, a Bioreductively Activated Nitric Oxide Prodrug
Kavita Sharma, Aishwarya Iyer, Kundan Sengupta, and Harinath Chakrapani*
Org. Lett. 2013, 15, 2636-2639
2018
Ryan J Holland, Anna E Maciag, Joseph E Saavedra, Larry K Keefer, and Harinath Chakrapani*
Journal of Chemical Crystallography, 2013, 43, 123–126
2018
Benzosultines as Sulfur Dioxide (SO2) Donors
Satish R. Malwal, Mahesh Gudem, Anirban Hazra,* and Harinath Chakrapani*
Org. Lett. 2013, 5, 1116-1119
2012
2018
Cross-Linking Protein Glutathionylation Mediated by O2-Arylated Bis-Diazeniumdiolate “Double JS-K”
Ryan J. Holland*, Anna E. Maciag, Varun Kumar, Lei Shi, Joseph E. Saavedra, Robert K. Prud'homme, Harinath Chakrapani, and Larry K. Keefer
Chem. Res. Toxicol. 2012, 25, 2670-2677
2018
Bioreductively-Activated Prodrugs of Nitric Oxide (NO)
Harinath Chakrapani, and Kavita Sharma
Free Radical Biology and Medicine, 2012, 53, S179
2018
Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones
Vinayak S. Khodade, Allimuthu T. Dharmaraja, Harinath Chakrapani*
Bioorganic & Medicinal Chemistry Letters, 2012, 3766-3769
2018
Synthesis and antimycobacterial activity of prodrugs of sulfur dioxide (SO2)
Satish R. Malwal, Dharmarajan Sriram, Perumal Yogeeswari, and Harinath Chakrapani*
2018
Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors
AT Dharmaraja, Alvala, Sriram, Yogeeswari, Chakrapani*
Chem. Commun., 2012, 48, 10325–10327
2018
Synthesis, thiol-mediated reactive oxygen species generation profiles and anti-proliferative activities of 2,3-epoxy-1,4-naphthoquinones
Med. Chem. Commun., 2012, 3, 219
2012
2018
Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO2) as Antimycobacterial Agents
Satish R. Malwal, Dharmarajan Sriram, Perumal Yogeeswari, V. Badireenath Konkimalla, and Harinath Chakrapani*
J. Med. Chem. 2012, 55, 553-557
PhD and Post-doc Publications of Dr. Harinath Chakrapani
1) Holland, R.; Maciag, A. E.; Kumar, V.; Shi, L.; Saavedra, J. E.; Prud'homme, R.; Chakrapani, H.; Keefer, L. K. “Crosslinking Protein Glutathionylation Mediated by O2-Arylated Bis-Diazeniumdiolate "Double JS-K"” Chemical Research in Toxicology, 2012, 25, 2670-2677.
2) Deschamps, J. R.; Saavedra, J. E. Cao, Z.; Keefer, L. K.; Chakrapani, H. “Stereochemical Origins of Chromophore Extension in O2-Substituted Diazeniumdiolates, Prodrugs of Nitric Oxide” Journal of Chemical Crystallography, 2013, 43, 123-126.
3) Maciag, A. E.; Holand, R. J.; Saavedra, J. E.; Chakrapani, H.; Shami, P. J.; Keefer, L. K. “Thiol Modification By Pharmacologically Active Agents of the Diazeniumdiolate Class” Forum on Immunopathological Diseases and Therapeutics 2012, 3, 91-95.
4) Maciag, A. E.; Nandurdikar, R. S.; Hong, S. Y.; Chakrapani, H.; Morris, N. L.; Diwan, B.; Shami, P. J.; Shiao, Y-H.; Anderson, L. M.; Keefer, L. K.; Saavedra, J. E. “Activation of the c-Jun N-terminal Kinase /Activating Transcription Factor 3 (ATF3) Pathway Characterizes Effective Arylated Diazeniumdiolate-Based Nitric Oxide-Releasing Anticancer Prodrugs” Journal of Medicinal Chemistry 2011, 54, 7751-7758.
5) Hong, S. Y.; Borchert, G. L.; Maciag, A. E.; Nandurdikar, R. S.; Saavedra, J. E.; Keefer, L. K.; Phang, J. M.; Chakrapani, H. “The Nitric Oxide Prodrug V-PROLI/NO Inhibits Cellular Uptake of Proline” ACS Medicinal Chemistry Letters, 2010, 1, 386–389.
6) Kumar, V.; Hong, S. Y.; Maciag, A. E.; Saavedra, J. E.; Adamson, D.; Prud'homme, R.; Keefer, L. K.; Chakrapani, H. "Stabilization of the Nitric Oxide (NO) Prodrugs and Anti-Cancer Leads, PABA/NO and Double JS-K through Incorporation into PEG-Protected Nanoparticles" Molecular Pharmaceutics 2010, 7, 291-298.
7) Nandurdikar, R. S.; Maciag, A. E.; Hong, S. Y.; Chakrapani, H.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. "Glycosylated PROLI/NO Derivatives as Nitric Oxide Prodrugs" Organic Letters, 2010, 12, 56–59.
8) Maciag, A. E.; Chakrapani, H.; Saavedra, J. E.; Morris, N. L.; Holland, R. J.; Kosak, K. M.; Shami, P. J.; Anderson, L. M.; Keefer, L. K.“The Nitric Oxide Prodrug JS-K is Effective Against Non-small Cell Lung Cancer Cells in vitro and in vivo : Involvement of Reactive Oxygen Species” Journal of Pharmacology and Experimental Therapeutics 2011, 336, 313-320.
9) Rai, G.; Sayed, A. A.; Lea, W. A.; Luecke, H.; Chakrapani, H.; Prast-Nielsen, S.; Jadhav, A.; Leister, W.; Shen, M.; Inglese, J.; Austin, C. P.; Keefer, L. K.; Arnér, E. S. J.; Simeonov, A.; Maloney, D. J. Williams, D. L.; Thomas, C. J. "Structure-Mechanism Insights and the Role of Nitric Oxide Donation Guide the Development of Oxadiazole-2-Oxides as Therapeutic Agents against Schistosomiasis" Journal of Medicinal Chemistry 2009, 52, 6474-6483.
10) Maciag, A. E.; Saavedra, J. E.; Chakrapani, H. "The Nitric Oxide Prodrug JS-K and its Structural Analogues as Cancer Therapeutic Agents" Anti-Cancer Agents in Medicinal Chemistry 2009, 9, 798-803.
11) Hong, S. Y.; Nandurdikar, R. S.; Saavedra, J. E.; Keefer, L. K.; Chakrapani, H."An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide prodrug" Tetrahedron Letters 2009, 50, 4545-4548.
12) Nandurdikar, R. S.; Maciag, A. E.; Citro, M. L.; Shami, P. J.; Keefer, L. K.; Saavedra, J. E.; Chakrapani, H. "Piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound" Bioorganic and Medicinal Chemistry Letters 2009, 19, 2760-2762.
13) Hong, S. Y.; Saavedra, J. E.; Keefer, L. K.; Chakrapani, H. "Improved Synthesis of V-PYRRO/NO, a Liver-Selective Nitric Oxide Prodrug" Tetrahedron Letters 2009, 50, 2069-2071.
14) Chakrapani, H.; Bartberger, M. D.; Toone, E. J. "C-Nitroso donors of Nitric Oxide" The Journal of Organic Chemistry 2009, 74, 1450-1453.
15) Andrei, D. A.; Maciag, A. E.; Chakrapani, H.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. " Aryl-bis(Diazeniumdiolates): Potent Inducers of S-Glutathionylation of Cellular Proteins and Their in Vitro Anti-proliferative Activities" Journal of Medicinal Chemistry 2008, 51, 7944-7952.
16) Chakrapani, H.; Maciag, A. E.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. "Cell-permeable Esters of Diazeniumdiolate Nitric oxide Prodrugs" Organic Letters 2008, 10, 5155-5158.
17) Chakrapani, H.; Kalathur, R. C.; Maciag, A. E.; Citro, M. L.; Ji, X.; Keefer, L. K.; Saavedra, J. E. "Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase activated nitric oxide prodrugs" Bioorganic and Medicinal Chemistry 2008, 16, 9764-9771.
18) Chakrapani, H.; Goodblatt, M. G.; Udupi, V.; Malaviya, S.; Shami, P. J.; Keefer, L. K.; Saavedra, J. E. "Synthesis and In Vitro Anti-Leukemic Activity of Structural Analogues of JS-K, An Anti-Cancer Lead Compound" Bioorganic and Medicinal Chemistry Letters 2008, 18, 950-953.
19) Chakrapani, H.; Wilde, T. C.; Citro, M. L.; Goodblatt, M. G.; Keefer, L. K.; Saavedra, J. E. "Synthesis and Studies of Structural Analogues of PABA/NO, an Anti-Cancer Lead Compound" Bioorganic and Medicinal Chemistry 2008, 16, 2657-2664.
20) Chakrapani, H.; Showalter, B. M.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. "Nitric Oxide Prodrugs: Diazeniumdiolates of Hindered Secondary Amines" Organic Letters 2007, 9, 4551-4554.
21) Chakrapani, H.; Showalter, B. M.; Kong, L.; Keefer, L. K.; Saavedra, J. E. "V-PROLI/NO, a Prodrug of the Nitric Oxide donor, PROLI/NO" Organic Letters 2007, 9, 3409-3412.
22) Chakrapani, H.; Gorczynski, M. J.; King, S. B. "Allylic Nitro Compounds as Nitrite Donors" Journal of the American Chemical Society 2006, 128, 16332-16337.
23) Pamula, V. K.; Srinivasan, V.; Chakrapani, H.; Fair, R. B.; Toone, E. J. "A Droplet-based Lab-on-a-chip for Colorimetric Detection of Nitroaromatic Explosives" Proceedings of the 18th IEEE International Conference on Micro Electro Mechanical Systems 2005, 722-725.
24) Gooden, D. M.; Chakrapani, H.; Toone E. J. "C-Nitroso Compounds: Synthesis, Physicochemical Properties and Biological Activities" Current Topics in Medicinal Chemistry 2005, 5, 687-705.
25) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. "Enantioselective Cyclization/Hydrosilylation of 1,6-Enynes Catalyzed by a Cationic Rhodium Bis(phosphine) Complex" Organic Letters 2003, 5,157-159.
26) Wang, X.; Chakrapani, H.; Madine, J. M.; Keyerleber, M. A.; Widenhoefer, R. A. "Cyclization/ Hydrosilylation of Functionalized 1,6-Diynes Catalyzed by Cationic Platinum Complexes Containing Bidentate Nitrogen Ligands" The Journal of Organic Chemistry 2002, 67, 2778-2788.
27) Wang X.; Chakrapani, H.; Stengone C. N.; Widenhoefer R. A. "Synthesis of Carbobicyclic Compounds via Palladium-Catalyzed Cyclization/Hydrosilylation: Evidence for Reversible Silylpalladation" The Journal of Organic Chemistry 2001, 66, 1755-1760.